1,2-Dichloroethane → Pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

HRID 55772Notes

Reaction equation

HRID 55772 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].C(Cl)C[Cl:15].Cl.[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[CH:20]([CH2:26][C:27](O)=[O:28])[CH2:19]2>C(N(CC)C(C)C)(C)C.ClCCl>[ClH:15].[N:18]12[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25]1)[CH:20]([CH2:26][C:27]([O:8][C:7]1[C:2]([F:1])=[C:3]([F:12])[C:4]([F:11])=[C:5]([F:10])[C:6]=1[F:9])=[O:28])[CH2:19]2

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 230241472-(Quinuclidin-3-yl)acetic acid hydrochloride

Product 1

HCID 86610796Pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

358 mg (1.94 mmol) of pentafluorophenol, 120.5 mg (0.63 mmol) of EDC and 1 drop of N,N-diisopropylethylamine are added to a solution of 100 mg (0.49 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride in 4 ml of dichloromethane at 0° C. The mixture is stirred at room temperature for 18 h. The contents of the flask are concentrated in vacuo and dried under high vacuum. The resulting crude product is employed without further purification in the following stages.

Workup

  1. concentrationThe contents of the flask are concentrated in vacuo
  2. customdried under high vacuum
  3. customThe resulting crude product is employed without further purification in the following stages

Sources & evidence

ORD record
ord-b3b1aaa0e07f4281b55d14c723e1b6a1
Source dataset
uspto-grants-2016_09
Patent number
US09433614B2

Reaction notes

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